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Internet Advertising Pioneer: Kevin O’Connor, Founder of DoubleClick and FindTheBest (Part 6)

Sramana: How do you determine a non-linear career path? What is that conversation like?

Kevin O’Conn0r: Organizations go through different stages. If you are in an early stage, then an individual’s career development is in his or her hands. When you get to a bigger company, career paths become far more linear. It is very difficult to become a VP in six months when there are a thousand people in the organization. In a startup, that is completely possible. When you are a startup and you have someone who comes in willing to work for less because they have equity, and they are willing to sleep in the backyard if needed, and they are willing to do whatever needs to be done, then you have a match for a startup environment. >>>

Internet Advertising Pioneer: Kevin O’Connor, Founder of DoubleClick and FindTheBest (Part 5)

Sramana: Part of the advantage in vertical search is the ability to zero in on a market segment using a precise taxonomy.

Kevin O’Connor: Absolutely. That is why we built a platform that lets us handle virtually any taxonomy. If you look at shopping comparison engines, you will see they are a price comparison engine, which makes them weak. We pull out a taxonomy for a product or service that goes beyond price.

Sramana: Do you run different sites for different verticals?

Kevin O’Connor: We do. FindTheBest is for products and services. FindTheCompany is for accessing and sharing information about companies. FindTheBest is our flagship. >>>

Internet Advertising Pioneer: Kevin O’Connor, Founder of DoubleClick and FindTheBest (Part 4)

Sramana: One of the core philosophies of our incubator is that over 99% of business that seek venture or angel financing get rejected. In the reject pool, there are a lot of solid mid-sized businesses. They will not be massive, but they can be solid profitable businesses.

Kevin O’Connor: I agree. Every top VC going today wants to see a billion-dollar business. I think a lot of people would be happy coming up with a $10 million company or a $100 million company. >>>

Internet Advertising Pioneer: Kevin O’Connor, Founder of DoubleClick and FindTheBest (Part 3)

Sramana: At that time people were still doing concept financing. The Internet happened because of concept financing. I wonder if the Internet would ever have happened if we did not have concept financing.

Kevin O’Connor: I’m not sure I agree. Eventually everything shakes out in a capitalistic market. It took a bit longer for things to shake out in the Internet because there was so much of a fake economy there. One of the phrases I hated most about the Internet was “the new economy” because that implied you did need to have profits. The value of a company was based on revenue. That created a fake economy. >>>

Internet Advertising Pioneer: Kevin O’Connor, Founder of DoubleClick and FindTheBest (Part 2)

Sramana: How did DoubleClick get off the ground?

Kevin O’Connor: When we started it in my basement we called in Internet Advertising Federation. We later changed it to Internet Advertising Network. We were developing the technology. While Dwight was building the technology, I was researching. We did not know anything about advertising or direct response. I picked up some of the classic works in those areas and realized that all of the advertising theories that had been developed over the past 50 years could actually be implemented in software. >>>

Student Entrepreneur to $10M Revenue Run Rate: Extrabux CEO Jeff Nobbs (Part 7)

Sramana: Do you have any unique challenges that you overcame? Most entreprenuers have a chicken and egg challenge that they have to overcome.

Jeff Nobbs: We definitely had a chicken and egg problem with our merchant relationships. To work with Victoria Secrets, JC Penny and others you have to be more than just a little startup company. It is hard to get traction without the big stores, and it’s hard to get big stores without the traction. We were fortunate to have started this in college because we had two slow years to gain that traction organically. We did not have spouses, kids and mortgages. >>>

Student Entrepreneur to $10M Revenue Run Rate: Extrabux CEO Jeff Nobbs (Part 6)

Sramana: When you had just five employees, were you all getting paid? Did you and your co-founder get paid?

Jeff Nobbs: My co-founder and I were barely getting paid. We were making minimum wage. We paid everyone else in equity and cash. Their salaries were a little under market, but not drastically. We made up for that with equity in the company. >>>

Student Entrepreneur to $10M Revenue Run Rate: Extrabux CEO Jeff Nobbs (Part 5)

Sramana: You said you raised a million dollars of funding. When did you raise that funding?

Jeff Nobbs: We raised money every few months for a couple of years. We have not raised money since 2011. Our valuation grew every time we raised money. We have a lot of shareholders now. Looking back, it would have been a lot easier if we had just raised one round. We were begging for money. >>>